How to Start a Conversation

3. Be Genuinely Curious and Interested in Other People

So once you’ve gathered your "intelligence," it’s easy to do the next step…be curious. The idea is to comment or a ask question, just be careful not to interrogate. The key is to be genuinely interested and inquisitive.

Mike Pratt, V.P. of Sales and marketing at Magnolia Hotels, says he loves to ask about people’s shoes because, he says, “If someone likes their shoes, it makes them feel good.” So I asked Mike his favorite shoe story and he told me about a gentleman he met while sitting on a plane.

He said, “He was wearing what was obviously a pair of expensive shoes. I mentioned how I liked his style of shoe and off went a two-hour conversation on where he got them, why, and how much they were, how they were made, etc. We then began a dialog about our professions, chatted the rest of the flight, and exchanged cards. Weeks later, I received by mail, a pair of the exact same shoes, in my size, from him…I called him to thank him and asked him why he sent such a nice gesture, as there was really no professional relationship that could have resulted from us meeting, and his response was, ‘I send something to everyone that I meet if I enjoyed meeting them. I enjoyed meeting you and you seem like someone who should have a nice pair of shoes.’”

Turns out the shoes were worth $1,200 bucks! Maybe I should have asked Mike about his shoes! Actually that reminds me of my final tip—try to practice every chance you get because it is a skill that can be cultivated. Practice at your favorite coffee shop, practice at sporting events, and of course you’d make my mother proud if you practiced while waiting in long grocery lines!